517-23-7

Basic information

• Product Name: 2-Acetylbutyrolactone
• Synonyms: -(-2-Hydroxyethyl)acetoaceticacid-lactone;2-Acetyl-4-hydroxybutyric acid gamma-lactone;2-Acetylbutyrolacton;2-Oxo-3-acetyltetrahydrofuran;3-Acetyl-2-(3H)-4,-5-dihydrofuranone;3-Acetyl-2(3H)-4,5-dihydrofuranone;3-acetyldihydro-2(3h)-furanon;3-Acetyltetrahydro-2-furanone
• CAS NO: 517-23-7
• Molecular Formula: C₆H₈O₃
• Molecular Weight: 128.13
• EINECS: 208-235-2
• Product Categories: ketone;Furan&Benzofuran;Carbonyl Compounds;Lactones;Organic Building Blocks;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Organic solvents
• Mol File: 517-23-7.mol

Chemical Properties

• Melting Point: <25 °C
• Boiling Point: 107-108 °C5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear/Liquid
• Density: 1.19 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0186mmHg at 25°C
• Refractive Index: n20/D 1.459(lit.)
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility: 200g/l
• PKA: 12.00±0.20(Predicted)
• Water Solubility: 310 g/L (20 ºC)
• Stability: Stable. Incompatible with strong oxidizing agents, strong bases.
• Merck: 14,83
• BRN: 112676
• CAS DataBase Reference: 2-Acetylbutyrolactone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Acetylbutyrolactone(517-23-7)
• EPA Substance Registry System: 2-Acetylbutyrolactone(517-23-7)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-61
• Safety Statements: 26-36-37/39-45-53
• WGK Germany: 1
• RTECS: LU3456000
• TSCA: Yes
• Hazardous Substances Data: 517-23-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Acetylbutyrolactone is used as an intermediate in the synthesis of various pharmaceutical products. It plays a crucial role in the production of pilocarpine, a leading therapeutic agent for the treatment of narrow and wide-angle glaucoma. 2-Acetylbutyrolactone's ability to participate in different chemical reactions makes it a valuable component in the development of new drugs and medications.
Used in Chemical Synthesis:
2-Acetylbutyrolactone is used as an intermediate in the synthesis of chemical products such as 2,4-disubstituted pyridines and 3,4-disubstituted pyridines. These compounds have various applications in the chemical industry, including the production of dyes, pigments, and other specialty chemicals.
Used in Fluorogenic Reagents:
2-Acetylbutyrolactone is used as a fluorogenic reagent in the quantitative spectrofluorometric determination of primary amines. This application demonstrates the compound's versatility and its ability to be used in analytical chemistry for the detection and quantification of specific chemical species.
Used in Synthesis of 5-(β-Hydroxethyl)-4-Methylthiazole:
2-Acetylbutyrolactone is used as a key intermediate in the synthesis of 5-(β-Hydroxethyl)-4-Methylthiazole, a compound with potential applications in the pharmaceutical and chemical industries.

Reference

Asghari, S.; Mohammadi, L., Reaction of tert-butyl isocyanide and dialkyl acetylenedicarboxylates in the presence of 2-acetylbutyrolactone. Synthesis of functionalized alpha-methylene-gamma-butyrolactones. Tetrahedron Lett. 2006, 47, 4297-4299. Rao, V. R.; Kumar, P. V., Facile one-pot synthesis of 3-{25-hydroxy-4-(2-hydroxy-ethyl)-3-methyl-pyrazol-1-yl -thiazol-4-yl} -chromen-2-ones via a three-component reaction. Synth. Commun. 2006, 36, 2157-2161. Horne, D. A.; Fugmann, B.; Yakushijin, K.; Buchi, G., A SYNTHESIS OF PILOCARPINE. J. Org. Chem. 1993, 58, 62-64. Sabry, S. M., Application of 2-acetylbutyrolactone to spectrofluorinietry: Fluorescence properties of Schiff bases derived from 2-acetylbutyrolactone and spectrofluorimetric determination of primary amine-containing compounds. J. Pharm. Biomed. Anal. 2006, 40, 1057-1067.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C6H8O3/c1-4(7)5-2-3-9-6(5)8/h5H,2-3H2,1H3/t5-/m0/s1

Synthetic route

α-acetyl-γ-butyrolactone sodium → acetamide (60-35-5) + 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7)

Conditions	Yield
With ethyl hydrazine hydrochloride In methanol at 10 - 20℃; for 2h; Temperature;	A 98.9% B 98.29%

4-butanolide (96-48-0) + acetic acid methyl ester (79-20-9) → 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7)

Conditions	Yield
Stage #1: 4-butanolide; acetic acid methyl ester With sodium methylate In methanol at 45 - 90℃; under 750.075 Torr; for 10h; Inert atmosphere; Large scale; Stage #2: With carbon dioxide In methanol; water at 0 - 35℃; under 6000.6 Torr; for 0.5h; Temperature; Pressure; Reagent/catalyst; Large scale;	96%

4-butanolide (96-48-0) + ethyl acetate (141-78-6) → 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7)

Conditions	Yield
With sodium ethanolate at 75℃; for 10h; Reflux;	93%
Stage #1: 4-butanolide; ethyl acetate With sodium methylate at 50 - 100℃; for 5h; Autoclave; Stage #2: With sulfuric acid at -5 - 5℃; for 5h; pH=6 - 7;	83%
With sodium at 80℃; for 8h; Mechanism;

4-butanolide (96-48-0) + acetaldehyde (75-07-0) → 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7)

Conditions	Yield
With sodium hydrogencarbonate In ethyl acetate at 60 - 95℃; under 750.075 - 7500.75 Torr; for 3.5h; Solvent; Temperature; Reagent/catalyst; Autoclave;	79.31%

oxirane (75-21-8) + acetoacetic acid methyl ester (105-45-3) → 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7)

Conditions	Yield
With sodium hydroxide In ethanol; water at -5 - 0℃; for 50h;	78%
With triethylamine In methanol at 5 - 95℃; under 1500.15 - 2250.23 Torr; for 2.15 - 5h; Product distribution / selectivity;	40.4%
With N,N,N',N'-tetramethylguanidine In methanol at 5 - 65℃; under 1500.15 - 2250.23 Torr; for 1.15 - 6.18333h; Product distribution / selectivity;	30.8%

4-butanolide (96-48-0) + acetic anhydride (108-24-7) → 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7)

Conditions	Yield
Stage #1: 4-butanolide With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.25h; Inert atmosphere; Stage #2: acetic anhydride In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;	42%

oxirane (75-21-8) + ethanol (64-17-5) + sodium ethyl acetylacetate enolate (1007476-32-5) → 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7)

oxirane (75-21-8) + sodium ethyl acetylacetate enolate (1007476-32-5) → 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7)

Conditions	Yield
With ethanol

ethanol (64-17-5) + sodium ethyl acetylacetate enolate (1007476-32-5) + 2-chloro-ethanol (107-07-3) → 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7)

oxirane (75-21-8) + ethyl acetoacetate (141-97-9) → 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7)

Conditions	Yield
With sodium hydroxide 1.) water, EtOH, 0 deg C, 30 min, 2.) 0 - 5 deg C, 72 h; Yield given. Multistep reaction;
With sodium hydroxide; sulfuric acid In water; ethylene glycol

4-butanolide (96-48-0) + sodium ethanolate (141-52-6) + ethyl acetate (141-78-6) → 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + 5-Hydroxy-2-pentanone (1071-73-4) + ethyl 4-hydroxybutanoate (999-10-0) + ethyl 4-(acetyloxy)butanoate (25560-91-2) + ethyl acetoacetate (141-97-9) + α-(2-Tetrahydrofuranylidene)-γ-butyrolactone (65652-24-6)

Conditions	Yield
at 100℃; under 1064 Torr; for 0.5h; Product distribution; various molar ratio of the reagents, other temp., other pressure, other time;

...Expand

4-butanolide (96-48-0) + acetyl chloride (75-36-5) → 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7)

Conditions	Yield
With 18-crown-6 ether 1.) THF, RT, 15 min, 2.) THF, RT, 3 h; Yield given. Multistep reaction;

3-<1-(N-phenylamino)-ethylidene>-4,5-dihydro-2(3H)-furanone (64620-59-3) → 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + aniline (62-53-3)

Conditions	Yield
With water at 25℃; Rate constant; Mechanism;

D-Glucose (2280-44-6) → 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7)

Conditions	Yield
With aluminium trichloride; Trioxane In methanol Dehydration; Heating;

4-butanolide (96-48-0) + ethyl acetate (141-78-6) → 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + acetoacetic acid ethyl ester and tetrahydro-<2,3'>bifuryliden-2'-one

Conditions	Yield
With sodium

hydrogenchloride (7647-01-0) + 2-acetyl-2-(methylsulfanyl-methyl)-succinic acid diethyl ester (412012-07-8) → 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + 3-methylene-4-oxopentanoic acid (89533-75-5) + 3--4-oxo-valeric acid

Conditions	Yield
10 h Erhitzen.;

4-butanolide (96-48-0) + C19H20ClNO4 (1258864-02-6) → 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78℃;

4-butanolide (96-48-0) + acetaldehyde (75-07-0) + ethyl acetate (141-78-6) → 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7)

Conditions	Yield
With sodium carbonate at 44 - 80℃; for 8.66667h; Temperature; Autoclave;

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + allyl bromide (106-95-6) → 3-(1-Hydroxy-1-methyl-but-3-enyl)-dihydro-furan-2-one

Conditions	Yield
With hydrogenchloride; indium In methanol; water for 10h; Ambient temperature;	100%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + 3-chloroprop-1-ene (107-05-1) → 3-(1-Hydroxy-1-methyl-but-3-enyl)-dihydro-furan-2-one

Conditions	Yield
With hydrogenchloride; indium In methanol; water for 10h; Ambient temperature;	100%
With tin In hydrogenchloride; methanol for 20h; Product distribution; Ambient temperature; other reagent, solvent, reaction time; also with allyl bromide;	90%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + chloro-trimethyl-silane (75-77-4) → 4-<1-(trimethylsiloxy)ethenyl>-5-(trimethylsiloxy)-2,3-dihydrofuran (133400-76-7)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; for 1h;	100%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) → 3-acetyl-3-chlorodihydrofuran-2(3H)-one (2986-00-7)

Conditions	Yield
With chlorine at -10℃; for 5h; Temperature; Saturated gas;	99.3%
With sulfuryl dichloride at 5 - 10℃; for 3h;	99.1%
With chlorine In dichloromethane at -10℃; for 5h; Temperature; Reagent/catalyst; Flow reactor;	99%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) → α-acetyl-α-hydroxy-γ-butyrolactone (135366-64-2)

Conditions	Yield
With 3,3-dimethyldioxirane; nickel diacetate In water; acetone for 3.5h; Ambient temperature;	99%
With 3,3-dimethyldioxirane In acetone at 20℃; for 72h;	98%
With samarium (III) iodide; iodine In tetrahydrofuran; water at 25℃; for 12h; Catalytic behavior; Green chemistry;	95%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + methyl vinyl ketone (78-94-4) → 3-acetyl-3-(3-oxobutyl)-4,5-dihydrofuran-2(3H)-one (58623-81-7, 74627-02-4, 176101-57-8)

Conditions	Yield
With silica gel In neat (no solvent) at 0 - 90℃; for 20h; Michael Addition;	99%
NDEAP grafted on silica In water at 80℃; for 0.233333h; Michael addition; microwave irradiation;	84%
With iron(III) chloride In dichloromethane at 20℃; Michael reaction;	36%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + benzylamine (100-46-9) → 2-<1-(N-benzylamino)ethylidene>butyrolactone

Conditions	Yield
With silica gel at 20℃; for 2h;	99%
With β‐cyclodextrin In water at 20℃; for 1.5h; chemospecific reaction;	96%
With cerium(III) chloride; tetrabutylammomium bromide at 20℃; for 0.0833333h;	95%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + chloro-trimethyl-silane (75-77-4) → 3-[1-[(trimethylsilyl)oxy]ethylidenyl]-4,5-dihydrofuran-2-one

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃;	99%
With triethylamine In benzene at 20℃; for 14h; Etherification;

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + rac-methylbenzylamine (618-36-0) → (Z)-3-[1-(1-phenylethylamino)ethylidene]tetrahydro-2-furanone

Conditions	Yield
With silica gel at 20℃; for 3.5h;	99%
at 23℃; for 4h;	89%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + methylamine (74-89-5) → 3-[1-Methylamino-eth-(Z)-ylidene]-dihydro-furan-2-one

Conditions	Yield
With silica gel at 20℃; for 4h;	99%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) → 2-(1-aminoethylidene)butyrolactone

Conditions	Yield
With ammonia; silica gel at 20℃; for 5h;	99%
With ammonium acetate; tetraethoxy orthosilicate In ethanol Heating;	98%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) → C6H7BF2O3

Conditions	Yield
With boron trifluoride diethyl etherate In toluene at 25℃; for 16h;	99%
With boron trifluoride diethyl etherate In toluene at 25℃; for 24h;	99%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + nitrostyrene (5153-67-3) → 3-acetyl-3-(-2-nitro-1-phenylethyl)dihydrofuran-2(3H)-one

Conditions	Yield
With 1-[3,5-bis(trifluoromethyl)phenyl]-3-[(2S)-dimethylamino-(1S)-phenylpropyl]thiourea In diethyl ether at 0℃; for 17h; nitro-Michael reaction; enantioselective reaction;	99%
With 3-((3,5-bis(trifluoromethyl)benzyl)amino)-4-((2-(dimethylamino)ethyl)-amino)cyclobut-3-ene-1,2-dione In toluene at 25℃; for 24h; Michael Addition; Inert atmosphere;	87%
(3ξ,8α,9R)-cinchonan-6',9-diol In tetrahydrofuran at 20℃; for 0.5h; Product distribution / selectivity; Michael Condensation;
With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane at 20℃; Michael Addition;
With 1,4-diaza-bicyclo[2.2.2]octane In neat (no solvent) at 20℃; Michael Addition;

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + 1,2-diamino-benzene (95-54-5) → (Z)-3-[1-(2-aminophenylamino)ethylidene]dihydrofuran-2(3H)-one

Conditions	Yield
In ethanol at 20℃; for 24h;	99%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) → C6H7ClO3*ClH

Conditions	Yield
With chlorine at 25 - 45℃; under 760.051 - 1520.1 Torr; for 2h; Temperature; Pressure; Concentration;	98.6%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + C12H12N2O3 (101561-12-0) → 7-Benzoylamino-6-hydroxy-6,8-dimethyl-1-oxo-2-oxa-7-aza-spiro[4.4]non-8-ene-9-carboxylic acid methyl ester

Conditions	Yield
In tetrahydrofuran for 0.1h; Ambient temperature;	98%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) → (-)-syn-(3R,1'R)-α-(hydroxyethyl)-γ-butyrolactone (155321-91-8)

Conditions	Yield
In N,N-dimethyl-formamide under 375030 Torr; Ambient temperature; Saccharomyces cerevisiae ML29;	98%
In N,N-dimethyl-formamide at 26℃; for 24h; Yarrowia lipolytica Y5;	95%
With nicotinic acid; ammonium sulfate; potassium dihydrogenphosphate; 5-hydroxy-6-methyl-3,4-pyridinedimethanol; D-glucose; D-myo-inositol; vitamin B1; boric acid; calcium (R)-pantothenate; magnesium sulfate; copper(II) sulfate; zinc(II) sulfate; potassium iodide; calcium chloride; manganese(ll) chloride; iron(II) chloride; biotin In ethanol; water at 29℃; for 96h; Yarrowia lipolytica PFL9CE;	69%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + acrylic acid methyl ester (292638-85-8) → 3-acetyl-2-oxotetrahydrofuran-3-propanoic acid methyl ester (280568-02-7)

Conditions	Yield
With polystyrene supported P1 iminophosphorane P-BEMP In tetrahydrofuran at 20℃; for 3h; Michael addition;	98%
With sodium hydride In tert-butyl alcohol at 35℃; for 4h; Michael addition;	96%
With 1,4-diaza-bicyclo[2.2.2]octane; water at 20℃; Michael addition;	95%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + 4-chloro-aniline (106-47-8) → 3-[(Z)-1-(4-chloro-anilino)-ethylidene]-dihydro-furan-2-one (64620-30-0)

Conditions	Yield
With cerium(III) chloride; tetrabutylammomium bromide at 20℃; for 0.0833333h;	98%
With β‐cyclodextrin In water at 20℃; for 0.333333h; chemospecific reaction;	95%
With tris(trifluoroacetato)bismuth(III); tetrabutylammomium bromide at 20℃; for 0.0833333h;	93%
cerium(III) chloride In water at 20℃; for 0.0833333h;	88%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + 4,4'-oxydiphenylene diamine (101-80-4) → C24H24N2O5

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 12h; Heating;	98%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + 3-amino-4,6-dimethylpyrazolo[3,4-b]pyridine (41601-44-9) → 3-(2-hydroxyethyl)-2,8,10-trimethylpyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidin-4-ol (1220997-01-2)

Conditions	Yield
In diphenylether at 220 - 225℃; for 0.25h;	98%

1-Phenylprop-1-yne (673-32-5) + 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) → 3-acetyl-3-(1-phenylallyl)dihydrofuran-2(3H)-one + α-acetyl-α-(trans-cinnamyl)-γ-butyrolactone

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; bis[2-(diphenylphosphino)phenyl] ether; ytterbium(III) triflate In 1,2-dichloro-ethane at 70℃; for 48h; Schlenk technique; Inert atmosphere; Glovebox; Sealed tube; diastereoselective reaction;	A 98% B n/a

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) → Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
With sodium iodide at 192℃; under 4500.45 Torr; Reagent/catalyst; Temperature; Pressure;	97.12%
Stage #1: 3-acetyl-2-oxo-4,5-dihydrofuran With hydrogenchloride In water at 100℃; for 2h; Stage #2: With sodium hydroxide In water at 80 - 100℃; for 2h;	90.2%
With 1-methyl-pyrrolidin-2-one; sodium iodide at 170℃; for 3h;	59%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + methyl 2-bromoacrylate (4519-46-4) → methyl 1-methylene-6-oxo-2,7-dioxaspiro[4,4]nonane-3-carboxylate

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran Ambient temperature;	96%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at -78 - -50℃; for 2h; domino Michael-O-alkylation;	96%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + p-toluidine (106-49-0) → 3-[(Z)-1-(4-toluidino)ethylidene]-dihydro-furan-2-one (64620-32-2)

Conditions	Yield
With β‐cyclodextrin In water at 20℃; for 1h; chemospecific reaction;	96%
ammonium cerium(IV) nitrate at 20℃; for 1.16667h;	95%
zirconium(IV) chloride at 20℃; for 0.5h;	92%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + ethanolamine (141-43-5) → 3-[1-(2-hydroxyethylamino)ethylidene]tetrahydrofuran-2-one

Conditions	Yield
With tris(trifluoroacetato)bismuth(III); tetrabutylammomium bromide at 20℃; for 0.166667h;	96%
With β‐cyclodextrin In water at 20℃; for 1.33333h; chemospecific reaction;	95%
With tris(trifluoroacetato)bismuth(III) In water at 20℃; for 10h;	93%
With cerium(III) chloride; tetrabutylammomium bromide at 20℃; for 0.0833333h;	92%
cerium(III) chloride In water at 20℃; for 0.166667h;	85%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + (E)-2-bromo-β-nitrostyrene (65185-68-4) → 3-acetyl-3-(1-(2-bromophenyl)-2-nitroethyl)dihydrofuran-2(3H)-one

Conditions	Yield
With 3-((3,5-bis(trifluoromethyl)benzyl)amino)-4-((2-(dimethylamino)ethyl)-amino)cyclobut-3-ene-1,2-dione In toluene at 25℃; for 24h; Michael Addition; Inert atmosphere;	96%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + methyl iodide (74-88-4) → 3-acetyl-3-methyl-dihydro-furan-2-one (1123-19-9, 112607-28-0, 112607-29-1)

Conditions	Yield
With potassium carbonate In acetone at 50℃; for 16h; Large scale;	95%
Stage #1: 3-acetyl-2-oxo-4,5-dihydrofuran With sodium methylate In benzene Stage #2: methyl iodide Further stages.;	83%
With potassium carbonate In acetone	80%

Upstream product

• 75-21-8 oxirane 
• 64-17-5 ethanol 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 96-48-0 4-butanolide 
• 141-52-6 sodium ethanolate 
• 141-78-6 ethyl acetate 
• 75-36-5 acetyl chloride 
• 64620-59-3 3-<1-(N-phenylamino)-ethylidene>-4,5-dihydro-2(3H)-furanone 
• 2280-44-6 D-Glucose 
• 7647-01-0 hydrogenchloride 
• 412012-07-8 2-acetyl-2-(methylsulfanyl-methyl)-succinic acid diethyl ester 
• 79-20-9 acetic acid methyl ester 
• 75-07-0 acetaldehyde 
• 108-24-7 acetic anhydride 

Downstream Products

• 1679-47-6 3-methyltetrahydro-2-furanone 
• 32595-98-5 4,5-Dihydro-2-methyl-3-furancarbonsaeure-methylester 
• 64745-38-6 3-[1-(2,5-dichloro-phenylimino)-ethyl]-dihydro-furan-2-one 
• 5400-68-0 2-(hydroxyimino)-γ-butyrolactone 
• 24186-16-1 2-phenylhydrazono-γ-butyrolactone 
• 740845-82-3 4-(2-hydroxy-ethyl)-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one 
• 108819-18-7 6-methoxy-4-methyl-2,3-dihydro-thieno[3,2-c]quinoline 
• 64745-43-3 3-[1-(2-methoxy-phenylimino)-ethyl]-dihydro-furan-2-one 
• 121233-09-8 4,6,8-trichloro-3-(2-chloro-ethyl)-2-methyl-quinoline 
• 64745-28-4 3-(1-p-tolylimino-ethyl)-dihydro-furan-2-one 
• 64745-37-5 3-[1-(4-chloro-phenylimino)-ethyl]-dihydro-furan-2-one 
• 91093-05-9 3-(4-nitro-benzoyl)-dihydro-furan-2-one 
• 6940-45-0 5-(2-hydroxyethyl)-6-methyl-2-aminouracil 
• 21585-16-0 5-(2-hydroxyethyl)-6-methyl-2-thiouracil 

Relevant articles and documents

Application of liquid sodium methoxide in synthesis of alpha-acetyl-gamma-butyrolactone and synthesis method of alpha-acetyl-gamma-butyrolactone

The invention provides application of liquid sodium methoxide in synthesis of alpha-acetyl-gamma-butyrolactone and a synthesis method of the alpha-acetyl-gamma-butyrolactone, and relates to the technical field of organic synthesis. The synthesis method of the alpha-acetyl-gamma-butyrolactone comprises the following steps: (a) performing pre-acylation reaction on an acetate compound and gamma-butyrolactone; (b) adding liquid sodium methoxide into the reaction liquid in the step (a) to carry out mixed reaction; (c) after the reaction in the step (b) is finished, concentrating and collecting methanol, and transferring the concentrated reaction liquid into an acylation kettle; (d) supplementing the acetate compound into the acylation kettle for acylation reaction; (e) performing neutralizing, filtering and concentrating to obtain an alpha-acetyl-gamma-butyrolactone crude product. According to the method, liquid sodium methoxide is used for replacing solid sodium methoxide for acylation synthesis, so that liquification and sealing of feeding are realized, the on-site feeding risk is reduced, and the synthesis yield is increased to 96% or above.

Preparation method of alpha-acetyl-gamma-butyrolactone

The invention relates to the field of organic synthesis, and discloses a preparation method of alpha-acetyl-gamma-butyrolactone. The method comprises the following steps: (1) gamma-butyrolactone, CH3COOR1 and R2ONa are subjected to acylation reaction to obtain a material containing alpha-acetyl-gamma-butyrolactone sodium salt, and R1 and R2 are respectively independently C1-C4 alkyl; and (2) in the presence of water, the material containing the alpha-acetyl-gamma-butyrolactone sodium salt is enabled to be in contact with CO2 gas to generate neutralization reaction. The method also has the advantage of higher yield under the condition of ensuring safety, and provides convenience for large-scale production of alpha-acetyl-gamma-butyrolactone.

Process for dissociating acetamidine hydrochloride with alpha-acetyl-gamma-butyrolactone sodium salt

The invention relates to the technical field of vitamin B synthesis intermediates, in particular to a process for dissociating acetamidine hydrochloride with alpha-acetyl-gamma-butyrolactone sodium salt. The process comprises the following steps: making alpha-acetyl-gamma-butyrolactone sodium salt react with the acetamidine hydrochloride and separating products to obtain acetamidine and alpha-acetyl-gamma-butyrolactone. According to the process, the intermediate product alpha-acetyl-gamma-butyrolactone sodium salt in the synthesis step of the alpha-acetyl-gamma-butyrolactone reacts with the acetamidine hydrochloride, the alpha-acetyl-gamma-butyrolactone sodium salt utilize hydrochloric acid coordinated in the acetamidine hydrochloride to achieve the effect that the alpha-acetyl-gamma-butyrolactone sodium salt produces the alpha-acetyl-gamma-butyrolactone, and the hydrochloric acid in the acetamidine hydrochloride is removed to form acetamidine. Synchronous production of two target products is achieved, the steps are saved, and the process is environmentally friendly and increases the revenue.

Preparation method for Alpha-acetyl-Gamma-butyrolactone

The invention discloses a preparation method for Alpha-acetyl-Gamma-butyrolactone, and belongs to the technical field of compound synthesis. The method comprises the following steps: under the conditions of an organic solvent, using Gamma-butyrolactone and acetaldehyde as initial raw materials, using inorganic base as a catalyst, performing an acetylation reaction, adjusting a pH value of reactionliquid by using diluted acid until the reaction liquid is neutralized, and post-processing to obtain the Alpha-acetyl-Gamma-butyrolactone. The method has the characteristics of economical feasibility, higher yield, safety and environmental protection, and is suitable for industrialization.

Method for preparing alpha-acetyl-gamma-butyrolactone

The invention discloses a method for preparing alpha-acetyl-gamma-butyrolactone. The method comprises the following steps: adding ethyl acetate and sodium carbonate into a three-necked flask, dropwiseadding gamma-butyrolactone at the temperature of 44 to 46 DEG C, stirring, mixing the ethyl acetate and liquid aldehyde, dropwise adding a reaction solution, uniformly mixing, stirring and reacting for 1.5 to 2.5 hours at the temperature of 54 to 58 DEG C, adding the reaction solution into a high-pressure kettle, reacting for 5 to 6 hours at the temperature of 80 to 85 DEG C, cooling to room temperature, adding the reaction solution into a three-necked flask, dropwise adding sulfuric acid at 3 to 5 DEG C to adjust the pH to be 6 to 7, precipitating solids in the dropwise addition process, after the addition is ended, stirring for 11 to 13 hours, re-testing the pH which is unchanged, filtering to remove the solids, washing a filter cake by using ethyl acetate, performing the decompressionrotary evaporation, removing the ethyl acetate until no fraction is outputted, obtaining a crude product, and performing the direct decompression rectification for the crude product. The preparation method is easy in obtaining raw materials, cheap in raw materials, easy in operation, higher in yield, and suitable for industrialized production.

Synthesis method for alpha-acetyl gamma-butyrolactone

The invention relates to the field of synthesis of organic intermediates of prothioconazole, in particular to a synthesis method for alpha-acetyl gamma-butyrolactone. The synthesis method includes thefollowing steps of (1) slowly heating a reactor to 75 DEG C, and adding gamma-butyrolactone, ethyl acetate and sodium ethoxide for reflux reaction for 10 hours to obtain a sodium salt of alpha-acetylgamma-butyrolactone and a by-product ethanol; (2) distilling the product obtained in the step (1) to remove the ethanol and excess ethyl acetate, adjusting the pH of the residue to 3-4 with dilute sulfuric acid, standing for liquid separation, removing aqueous phase, and performing vacuum distillation in an organic phase at a pressure of 0.1 MPa and a temperature of 65-70 DEG C to obtain alpha-acetyl gamma-butyrolactone. The synthesis method uses a reaction base material ethyl acetate as a base solvent and uses sodium ethoxide as a condensing agent, has mild reaction conditions and improved safety, avoids pollution caused by adopting additional solvents such as benzene solvent and the like, and has good safety, simple post-treatment method, high yield of alpha-acetyl gamma-butyrolactone above 90%, and high purity of alpha-acetyl gamma-butyrolactone above 98%.

Method for preparing alpha-acetyl-gamma-butyrolactone

The invention discloses a method for preparing alpha-acetyl-gamma-butyrolactone and relates to the technical field of chemical product preparation. The method comprises the following steps: by takingsolid sodium methoxide as a catalyst and gamma-butyrolactone and ethyl acetate as initial raw materials, implementing an acetylation reaction, after the reaction is completed, concentrating a reactionliquid, and separating an alpha-acetyl-gamma-butyrolactone sodium solid; implementing pulping and washing on the alpha-acetyl-gamma-butyrolactone sodium solid by using a second organic solvent in which the alpha-acetyl-gamma-butyrolactone sodium solid is not dissolvable; putting the washed alpha-acetyl-gamma-butyrolactone sodium solid into a third organic solvent, adjusting the pH value to 6-7 byusing an acid solution, stirring, filtering, and implementing vacuum distillation on filtrate, thereby obtaining alpha-acetyl-gamma-butyrolactone. The method has the characteristics of being short inpurification time, low in energy consumption, simple in preparation equipment, concise in operation, economically feasible, high in product purity, relatively high in yield, good in environment protection, and the like.

Catalytic decarboxylative alkenylation of enolates

A palladium-catalyzed decarboxylative alkenylation of stabilized enolates has been developed, which gives rise to alkenylated dicarbonyl products from enol carbonates regioselectively with concomitant installation of a quaternary all-carbon center. The broad scope of the reaction has been demonstrated by successfully utilizing a range of enolates and external phenol nucleophiles.

Mechanism of α-acetyl-γ-butyrolactone synthesis

The mechanism of α-acetyl-γ-butyrolactone (ABL) synthesis from γ-butyrolactone (GBL) and ethyl acetate (EtOAc) was explored by detecting the material changes involved and the enthalpies of formation of the synthons, products, and possible intermediates were calculated using the density functional theory. GBL forms a carbanion of γ-butyrolactone by losing an α-H under strongly alkaline conditions. ABL is then obtained via two reaction mechanisms. One of the reaction mechanisms involves direct reaction of the carbanion of GBL with EtOAc to produce ABL. The other involves the formation of a carbanion of α-(2-hydroxy-tetrahydrofuran-2-yl)-γ- butyrolactone through the reaction of two molecules of GBL, and the subsequent combination of this anion with EtOAc to produce ABL. ABL is thus formed through the above two kinds of competitive ester condensation reactions. It is unnecessary to take into account synthons' local thickness, and their self-condensation under these conditions. Both reactions of the carbanion of GBL with EtOAc and GBL are exothermic, so the control of their reaction rate is the key to their security. Considering the reasons above, this work applied synthon as the solvent, and avoided environmental pollution by alkylbenzene; also, accidents such as red material and fire were avoided by specific surface area of sodium metal control. Effective isolation of the organic and aqueous phases was performed using the salting out method. Thus, an environmentally friendly, safe, simple, and efficient new method for the synthesis of ABL with the yield higher than 90 % has been established.

An enantio-and diastereocontrolled synthesis of (-)-salinosporamide A

The enantio-and diastereocontrolled total synthesis of (-)-salinosporamide A, a potent 20S proteasome inhibitor, was accomplished through organocatalytic aldolization, diastereoselective Claisen condensation, a Rh-catalyzed Reformatsky reaction, and an AZADO-catalyzed oxidative β-lactonization reaction as the key reactions. The Japan Institute of Heterocyclic Chemistry.